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As Bobby lies in a coma after being shot by the leader of the Leviathans, Dick Roman, Bobby's reaper appears in his subconscious. Bobby has remembered how Rufus once told him that he came out of a coma – as his life flashed before him, in each memory there was a door to another memory, and that the way out, the way to wake up was through his worst memory. The reaper tells him he can't escape him.

Later, Bobby uses a spell to bind the reaper, but the reaper tells him the spell won't hold, as his brain is being killed by the damage from the bullet and his memories are disintegrating. He tells Bobby he has achieved much in his life, but also warns Bobby that if he doesn't go with him, he will remain trapped as a ghost. Bobby says he wants to stay to help Sam and Dean – "his boys."

After Bobby finally confronts his worst memory, he manages to wake for a moment to pass on the numbers which are a key to the leviathan's plot to Sam and Dean. Lapsing into unconsciousness again, the reaper again appears. He points out the darkness surrounding the room they are in – Bobby's memories are gone. He has only one left – a night watching Chuck Norris movies with Sam and Dean as they jokingly argue about movie snacks. The reaper opens his pocket watch and asks "Well, Bobby? Stay or go – what's it gonna be?"